Method for generating secondary phosphines

A method for generating a secondary phosphine from a secondary phosphine oxide comprising a reaction of the secondary phosphine oxide and a reducing agent comprisina an R1R2AlH moiety, wherein R1 and R2 are each an alkyl species or oxygen, and wherein at least one of R1 or R2 comprises at least 2 carbon atoms, further comprising the steps of:

• providing a quenching agent adapted to generate a neutralized aluminum by-product from the reducing agent that remains after the reaction of the secondary phosphine oxide and the reducing agent;
• isolating the secondary phosphine from (i) the neutralized aluminum by-product and (ii) water.

A method for generating a secondary phosphine from a secondary phosphine oxide comprisina a reaction of the secondary phosphine oxide and a reducing agent comprising an R1R2AlH moiety, wherein R1 and R2 are each an alkyl species or oxygen, and wherein at least one of R1 or R2 comprises at least 2 carbon atoms, wherein the step of reacting the secondary phosphine oxide with the reducing agent is anaerobic.

A method for generating a secondary phosphine from a secondary phosphine oxide comprising a reaction of the secondary phosphine oxide and a reducing agent comprising an R1R2AlH moiety, wherein R1 and R2 are each an alkyl species or oxygen, and wherein at least one of R1 or R2 comprises at least 2 carbon atoms, wherein the step of reacting the secondary phosphine oxide with the reducing agent is effectuated between about −25° C. to 50° C.

A method for generating a secondary phosphine from a secondary phosphine oxide comprising a reaction of the secondary phosphine oxide and a reducing agent comprising an R1R2AlH moiety, wherein R1 and R2are each an alkyl species or oxygen, and wherein at least one of R1 or R2 comprises at least 2 carbon atoms, wherein the step of reacting the secondary phosphine oxide with the reducing agent is effectuated at or below about −25° C.

A method for generating a secondary phosphine from a secondary phosphine oxide comprising the step of reacting the secondary phosphine oxide with a reducing agent comprising an R1R2R3Al moiety, wherein R1, R2, and R3 are not hydrogen, and wherein at least one of R1, R2, and R3 is an alkyl species comprising a β-hydrogen atom, not including triethylaluminum, wherein the secondary phosphine oxide is reacted with the reducing agent in a mixture comprising a solvent selected from the group consisting of:

• hydrocarbons, ethers, halocarbons, tetrahydrofuran, toluene, dioxane, xylene, hexane, heptane, cyclohexane, diethyl ether, dichloromethane, dichloroethane, 2-methyl-THF, MTBE, monoglyme, diglyme, triglyme, tetraglyme, chloroform, methylcyclohexane, octane, di-n-butylether, diisopropylether, ethylbenzene, cyclopentylmethylether, and combinations and mixtures thereof.

A method for generating a secondary phosphine from a secondary phosphine oxide comprising the step of reacting the secondary phosphine oxide with a reducing agent comprising an R1R2R3Al moiety, wherein R1, R2, and R3 are not hydrogen, and wherein at least one of R1, R2, and R3 is an alkyl species cormprising a β-hydrogen atom, not including triethylaluminum, further comprising the steps of:

• providing a quenching agent adapted to generate a neutralized aluminum by-product from the reducing agent that remains after the reaction of the secondary phosphine oxide and the reducing agent;
• isolating the secondary phosphine from (i) the neutralized aluminum by-product and (ii) water.

A method for generating a secondary phosphine from a secondary phosphine oxide comprising the step of reacting the secondary phosphine oxide with a reducing agent comprising an R1R2R3Al moiety, wherein R1,R2, and R3 are not hydrogen, and wherein at least one of R1, and R2, and R3 is an alkyl species comprising a β-hydrogen atom, not including triethylaluminum, wherein the step of reacting the secondary phosphine oxide with the reducing agent is anaerobic.

A method for generating a secondary phosphine from a secondary phosphine oxide comprising the step of reacting the secondary phosphine oxide with a reducing agent cormprising an R1R2R3Al moiety. wherein R1, R2, and R3 are not hydrogen, and wherein at least one of R1, R2, and R3 is an alkyl species comprising a β-hydrogen atom, not including triethylaluminum, wherein the step of reacting the secondary phosphine oxide with the reducing agent is effectuated between about −25° C. to 50° C.

A method for generating a secondary phosphine from a secondary phosphine oxide comprising the step of reacting the secondary phosphine oxide with a reducing agent comprising an R1R2R3Al moiety, wherein R1, R2, and R3 are not hydrogen, and wherein at least one of R1, R2, and R3 is an alkyl species comprising a β-hydrogen atom, not including triethylaluminum, wherein the step of reacting the secondary phosphine oxide with the reducing agent is effectuated at or below about −25° C.